Surfactants, as that term is generally known and used, are surface-active compounds characterized by certain defining features in structure and property. See, for example, 22 Kirk-Othmer Encyclopedia of Chemical Technology 332-36 (3d ed. 1979). Among such defining features, surfactants as a class are amphipathic in structure, composed of groups having opposing solubility tendencies. The most common surfactants are composed of two such groups, an oleophilic hydrocarbon chain and a water solubilizing ionic group. Surfactants are widely used throughout industry and enjoy a wide variety of application. Surfactants may be used for any application requiring those properties characteristic of surface-active agents: detergency, foaming, wetting, emulsifying, solubilizing, and dispersing.
A commercially-important class of surfactants comprises that containing one or more fluorochemical moieties and one or more water solubilizing polar moieties. Typically, such surfactants are formed by reacting one or more fluorochemical compounds with one or more water solubilizing compounds, where the fluorochemical compounds are formed as the product of a fluorination reaction of a hydrocarbon, typically alkyl, precursor. The fluorination reaction used to produce the fluorochemical intermediate compounds typically is carried out by electrochemical fluorination with hydrogen fluoride, and is less frequently carried out using direct fluorination with elemental fluorine. Electrochemical fluorination of ether-containing compounds, the preferred method of fluorination, is, however, generally characterized by low yield. See, e.g., T. Abe & S. Nagase, Electrochemical Fluorination (Simons Process) as a Route to Perfluorinated Organic Compounds of Industrial Interest, 19, 28-29 in PREPARATION, PROPERTIES AND INDUSTRIAL APPLICATIONS OF ORGANOFLUORINE COMPOUNDS (R. E. Banks ed., 1982), reporting yields of perfluorodialkyl ethers from their corresponding dialkyl ethers of much less than 50 percent, and Patricia M. Savu, Fluorinated Higher Carboxylic Acids, 11 KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY 551 (4th ed. 1994), noting generally poor yields obtained from the electrochemical fluorination of ethers.